Fiber-reactive azo dyes and dye mixtures, preparation thereof and use thereof

Abstract

The present invention relates to azo dyes of the formula (1) in which R, M, and Y are defined as stated in claim 1 , to dye mixtures comprising them, to processes for preparing them, and to their use.

1. An azo dye of the formula (1) 
       
         
           
           
               
               
           
         
         in which 
         Y is —CH═CH 2  or —CH 2 CH 2 Z, in which 
         Z is an alkali-detachable group; 
         R is a radical —COOR 1 , —CN or —CONR 2 R 3 , in which 
         R 1  is M or (C 1 -C 4 )-alkyl; 
         R 2  and R 3  independently of one another are hydrogen or (C 1 -C 4 )-alkyl; and 
         M is hydrogen, ammonium, an alkali metal, or the equivalent of an alkaline earth metal. 
       
     
     
       2. The azo dye as claimed in  claim 1 , wherein Y is vinyl, β-chloroethyl or β-sulfatoethyl. 
     
     
       3. The azo dye as claimed in  claim 1 , wherein R is —COOM or —CONH 2 , where M is hydrogen or sodium. 
     
     
       4. The azo dye as claimed in  claim 2 , wherein R is —COOM or —CONH 2 , where M is hydrogen or sodium. 
     
     
       5. A dye mixture which comprises the dye of the formula (1) as claimed in  claim 1  and at least one further fiber-reactive dye. 
     
     
       6. The dye mixture as claimed in  claim 5 , which comprises as further fiber-reactive dye a dye of the formula (2) 
       
         
           
           
               
               
           
         
         in which 
         A is 
       
       
         
           
           
               
               
           
         
         R 4  is hydrogen, methyl, methoxy or sulfo; 
         R 5  is hydrogen, acetyl or carbonylamido; 
         n is 0 or 1; 
         m is 0, 1, 2 or 3; 
         Z is an alkali-detachable group; 
         M is hydrogen, ammonium, an alkali metal, or the equivalent of an alkaline earth metal; and 
         Q is a radical of the formula (a), (b) or (c) 
       
       
         
           
           
               
               
           
         
         in which 
         X is halogen; 
         R 6  and R 7  are hydrogen, methyl or ethyl; and 
         M and Z are defined above. 
       
     
     
       7. The dye mixture as claimed in  claim 6 , X is fluoro or chloro. 
     
     
       8. The dye mixture as claimed in  claim 5 , which comprises as further fiber-reactive dye a dye of the formula (3) 
       
         
           
           
               
               
           
         
         in which 
         R 8  and R 9  independently of one another are hydrogen, methyl, ethyl, methoxy or ethoxy; 
         p is 0 or 1; 
         Z is an alkali-detachable group; 
         M is hydrogen, ammonium, an alkali metal, or the equivalent of an alkaline earth metal; and/or 
         a dye of the formula (4) 
       
       
         
           
           
               
               
           
         
         in which 
         R 10  and R 11  independently of one another are hydrogen, methyl, ethyl, methoxy or ethoxy; 
         q is 0 or 1; and 
         Z and M are defined as above. 
       
     
     
       9. A process for preparing the azo dye as claimed in  claim 1 , which comprises diazotizing a compound of the formula (5) 
       
         
           
           
               
               
           
         
         in which R is defined as stated in  claim 1  and then carrying out coupling onto a compound of the formula (6) 
       
       
         
           
           
               
               
           
         
         in which Y and M are defined as stated in  claim 1 . 
       
     
     
       10. A process for preparing the dye mixture as claimed in  claim 5 , which comprises mechanically mixing the individual dyes. 
     
     
       11. A method of dyeing or printing hydroxy- and/or carboxamido-containing material, which comprises applying one or more dyes as claimed in  claim 1  in dissolved form to the material and fixing the dye or dyes on the material by means
 of heat, 
 with the aid of an alkaline agent, or 
 by means of heat and with the aid of an alkaline agent. 
 
     
     
       12. A method of dyeing or printing hydroxy- and/or carboxamido-containing material, which comprises applying one or more dyes as claimed in  claim 4  in dissolved form to the material and fixing the dye mixture on the material by means
 of heat, 
 with the aid of an alkaline agent, or 
 by means of heat and with the aid of an alkaline agent. 
 
     
     
       13. An ink for digital textile printing by the inkjet process, which comprises the azo dye as claimed in  claim 1 . 
     
     
       14. An ink for digital textile printing by the inkjet process, which comprises the dye mixture as claimed in  claim 5 .